Organic electroluminescent material and device thereof

Abstract

The invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound with a structure shown in a formula 1, and the compound can be used as an electron blocking material and the like in an organic electroluminescent device. The compound can be used in an organic electroluminescent device, for example, as an electron blocking material and the like. When the compounds are applied to organic electroluminescent devices, the voltage of the devices can be reduced, the efficiency of the devices can be improved or high efficiency of the devices can be kept, particularly, the service lives of the devices can be greatly prolonged, and better comprehensive performance of the devices can be provided. Also disclosed are an organic electroluminescent device comprising the compound and a compound composition comprising the compound.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic electroluminescent devices, and more particularly to a compound having a structure of Formula 1, an organic electroluminescent device comprising the compound, and a compound composition comprising the compound. Background Art

[0002] Organic electronic devices include, but are not limited to, the following categories: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photoreceptors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasmonic light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0004] OLEDs can be categorized into three different types based on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. Triplet states generated in the device are wasted through non-radiative decay channels. As a result, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metal complexes as the emitter. This allows for the harvesting of both singlet and triplet states, achieving an IQE of 100%. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be categorized based on the form of the materials used, into small molecule and polymer OLEDs. A small molecule is any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights as long as they have a precise structure. Dendrimers, with their well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically produced by vacuum thermal evaporation. Polymer OLEDs are produced using solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be produced using solution methods if the material can be dissolved or dispersed in a solvent.

[0007] The luminescent color of OLEDs can be achieved through the structural design of luminescent materials. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life, and high operating voltage. Commercial full-color OLED displays generally adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which remains a problem. In addition, it is expected to have a more saturated luminescent spectrum, higher efficiency, and longer device life.

[0008] The voltage, efficiency, and other performance characteristics of organic electroluminescent devices are critically linked to the carrier concentration balance within the light-emitting layer. This balance can be more effectively controlled through the molecular design of charge transport and carrier blocking materials. Compounds containing spirosilane or nitrogen-containing spirocyclic structures have been reported as hole transport materials or electron blocking materials (luminescence-assisting materials) in electroluminescent devices.

[0009] WO2014017844A1 discloses a A compound of the structure wherein X is selected from C, O, P, S, Se or Si, and the compound is disclosed in the specific structure The compound is used as a host material in an electroluminescent device. This application does not disclose a compound containing both a spirosilylfluorene structure fragment and a nitrogen-containing spirocyclic structure fragment, and the two are connected at a specific position, nor does it disclose or teach the effect of the compound as other materials on device performance.

[0010] CN114790170A discloses a A compound of structure, wherein Ar2 has

[0011] The structure represented by the invention is that among the many specific structures disclosed, the silicon-containing compound is only compound This application does not disclose or teach a compound comprising both a spirosilylfluorene structural fragment and a nitrogen-containing spirocyclic structural fragment, wherein the two are linked at a specific position.

[0012] The applicant's previous patent application US2022359832A1 discloses an organic layer comprising a structure The first compound represented by the structure The application focuses on the application of the combination of the two compounds as a hole injection material, and does not focus on the application of the second compound as an electron blocking material. The application also does not disclose that the second compound contains a spirosilane structure fragment and a nitrogen-containing spirocyclic structure fragment at the same time, and the two are connected at a specific position.

[0013] As the industry's demand for the performance of organic electroluminescent devices continues to increase, OLED materials with excellent performance such as lower voltage, higher efficiency, longer life and good thermal stability still need in-depth research and development. Summary of the Invention

[0014] The present invention aims to provide a series of compounds comprising a spirosilylfluorene structure represented by Formula 1, connected to a nitrogen-containing spirocyclic structure at specific positions, to address at least some of the aforementioned problems. These compounds can be used in organic electroluminescent devices, for example, as electron-blocking materials. Application of these compounds in organic electroluminescent devices can reduce device voltage, improve device efficiency, or maintain high device efficiency. In particular, they can significantly extend device life and provide better overall device performance.

[0015] According to one embodiment of the present invention, a compound is disclosed, which has a structure represented by Formula 1:

[0016]

[0017] Among them, X1-X 15 Each occurrence is the same or different selection from CR x or N;

[0018] Ring A and Ring B are identical or different at each occurrence and are selected from an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof;

[0019] R y Each occurrence of the same or different means mono-, poly- or no-substitution;

[0020] R1, R2 are the same or different at each occurrence and are selected from substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 ring carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or a combination thereof; R1 and R2 can optionally be linked to form a ring;

[0021] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0022] T is selected from a single bond, -O-, -S-, -CR'R"-, -NR'-, -SiR'R"-, -GeR'R"- or -CR'=CR"-;

[0023] R x , R yR', R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0024] Adjacent substituent R x , R y , R', and R" can be optionally linked to form a ring.

[0025] According to another embodiment of the present invention, an organic electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the compound described in the above embodiment.

[0026] According to another embodiment of the present invention, a compound composition is also disclosed, which comprises the compound described in the aforementioned embodiment.

[0027] The present invention discloses a series of compounds comprising a spirosilylfluorene structural fragment represented by the structure of Formula 1, connected to a nitrogen-containing spirocyclic structural fragment at a specific position. These compounds can be used in organic electroluminescent devices, for example as electron-blocking materials, and can improve the performance of organic electroluminescent devices, for example, by reducing device voltage, increasing device efficiency, or maintaining high device efficiency. In particular, they can significantly increase device lifespan and enhance overall device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0029] Figure 2is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. DETAILED DESCRIPTION

[0030] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0031] There are many more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entireties. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0032] The above layered structures are provided by way of non-limiting examples. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired emission spectrum.

[0033] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. The organic layer can include one or more layers.

[0034] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is shown schematically and non-limitingly. Figure 1 The difference is that an encapsulation layer 102 can also be included above cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0035] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0036] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0037] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, the cathode may be described as being "disposed on" the anode even if various organic layers are present between the cathode and the anode.

[0038] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0039] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is not believed to contribute to the photoactive properties of the emissive material, but the ancillary ligand may modify the properties of the photoactive ligand.

[0040] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0041] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but relies on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap so as to convert between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by the triplet, the fraction of backfilling the singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the electrically generated excitons.

[0042] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Typically, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0043] Definition of Substituent Terms

[0044] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0045] Alkyl - as used herein, includes straight chain and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

[0046] Cycloalkyl - as used herein, includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.

[0047] Heteroalkyl - As used herein, a heteroalkyl group comprises one or more carbon atoms in the alkyl chain substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. The example of heteroalkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl can be optionally substituted.

[0048] Alkenyl - as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. Alkenyl groups can be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, alkenyl groups can be optionally substituted.

[0049] Alkynyl - as used herein, encompasses straight chain alkynyl groups. Alkynyl groups can be alkynyl groups comprising 2 to 20 carbon atoms, preferably alkynyl groups having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl, etc. are preferred. In addition, alkynyl groups can be optionally substituted.

[0050] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.

[0051] Heterocyclic group or heterocycle - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepine and tetrahydrothiol. Additionally, heterocyclyl groups may be optionally substituted.

[0052] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups may contain from 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group may have from 3 to 30 carbon atoms, preferably from 3 to 20 carbon atoms, and more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group comprises an oxadiazole, an isocyanine ...

[0053] Alkoxy - as used herein, is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclyl are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.

[0054] Aryloxy - As used herein, it is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenyloxy. In addition, the aryloxy group may be optionally substituted.

[0055] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, substituted alkyl.Alkyl group can be substituted alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl, alkyl,

[0056] Alkylsilyl - As used herein, encompasses alkyl-substituted silicon groups. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Additionally, the alkylsilyl group may be optionally substituted.

[0057] Arylsilyl - As used herein, encompasses silicon groups substituted with at least one aryl group. The arylsilyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilyl group may be optionally substituted.

[0058] Alkylgermanyl - As used herein, alkyl-substituted germanium groups are encompassed. The alkylgermanyl group can be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of alkylgermanyl groups include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-tert-butylgermanyl, triisobutylgermanyl, dimethyl-tert-butylgermanyl, and methyldi-tert-butylgermanyl. Additionally, the alkylgermanyl group can be optionally substituted.

[0059] Arylgermanyl - As used herein, encompasses germanium groups substituted with at least one aryl or heteroaryl group. The arylgermanyl group may be one having 6 to 30 carbon atoms, preferably one having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl, phenyldibiphenylgermanyl, diphenylbiphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, and diphenyltert-butylgermanyl. Additionally, the arylgermanyl group may be optionally substituted.

[0060] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., means that one or more CH groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives will readily occur to one of ordinary skill in the art, and all such analogs are intended to be included within the terminology described herein.

[0061] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid , substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphino group, refers to alkyl, cycloalkyl, heteroalkyl, heterocyclic group, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid group, ester group, sulfinyl, sulfonyl and phosphino group, any one of which may be selected from deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted alkyl having 6-30 carbon atoms aryl, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanyl having 3 to 20 carbon atoms, unsubstituted arylgermanyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0062] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attaching a fragment are considered equivalent.

[0063] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in compounds may be preferred because it enhances device efficiency and stability.

[0064] In the compounds described herein, multiple substitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its connected structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.

[0065] In the compounds mentioned in the present disclosure, unless clearly defined, such as adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including the situation where adjacent substituents can be connected to form a ring, and also including the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged ring, condensed ring, etc.), as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0066] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0067]

[0068] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other via a chemical bond to form a ring, as can be exemplified by the following formula:

[0069]

[0070] The statement that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to further distant carbon atoms are linked to each other by a chemical bond to form a ring, as can be exemplified by the following formula:

[0071]

[0072] Furthermore, the statement that adjacent substituents can optionally be linked to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0073]

[0074] According to one embodiment of the present invention, a compound is disclosed, which has a structure represented by Formula 1:

[0075]

[0076] Among them, X1-X 15 Each occurrence is the same or different selection from CR x or N;

[0077] Ring A and Ring B are identical or different at each occurrence and are selected from an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof;

[0078] R y Each occurrence of the same or different means mono-, poly- or no-substitution;

[0079] R1, R2 are the same or different at each occurrence and are selected from substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 ring carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or a combination thereof; R1 and R2 can optionally be linked to form a ring;

[0080] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0081] T is selected from a single bond, -O-, -S-, -CR'R"-, -NR'-, -SiR'R"-, -GeR'R"- or -CR'=CR"-;

[0082] R x , R yR', R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0083] Adjacent substituent R x , R y , R', and R" can be optionally linked to form a ring.

[0084] In this embodiment, "R1, R2 can be optionally linked to form a ring" is intended to indicate that R1 and R2 in Formula 1 can be bridged to form a ring. For example, the ring containing R1, R2 and T can be an adamantane ring. Here, * indicates the position where the adamantane ring is connected to ring A and ring B. Obviously, R1 and R2 may not be bridged to form a ring.

[0085] In this embodiment, the structure represented by the ring containing R1, R2 and T includes but is not limited to: * indicates the position where the adamantane ring is connected to ring A and ring B.

[0086] In this context, “the adjacent substituent R x , R y , R', R" can optionally be linked to form a ring", which is intended to indicate adjacent substituent groups, for example, two substituents R x Between the two substituents R y Between the substituents R' and R", any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.

[0087] According to one embodiment of the present invention, the compound has a structure represented by Formula 1-1:

[0088]

[0089] Among them, X1-X 15 Each occurrence is the same or different selection from CR x or N;

[0090] Ring A and Ring B are identical or different at each occurrence and are selected from an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof;

[0091] Ring C and Ring D are identical or different at each occurrence and are selected from a saturated carbocyclic ring having 3 to 20 carbon atoms, an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof;

[0092] R y , R z Each occurrence of the same or different means mono-, poly- or no-substitution;

[0093] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0094] T is selected from a single bond, -O-, -S-, -CR'R"-, -NR'-, -SiR'R"-, -GeR'R"- or -CR'=CR"-;

[0095] R x , R y , R zR', R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0096] Adjacent substituent R x , R y , R z , R', and R" can be optionally linked to form a ring.

[0097] In this context, “the adjacent substituent R x , R y , R z , R', R" can optionally be linked to form a ring", which is intended to indicate adjacent substituent groups, for example, two substituents R x Between the two substituents R y Between the two substituents R z Between the substituents R' and R", any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.

[0098] According to one embodiment of the present invention, wherein the ring A, ring B, ring C and ring D are identically or differently selected from an arylene group having 6 to 25 carbon atoms, a heteroarylene group having 3 to 25 carbon atoms, or a combination thereof.

[0099] According to one embodiment of the present invention, wherein the ring A, ring B, ring C and ring D are identically or differently selected from aromatic rings having 6-18 carbon atoms, heteroaromatic rings having 3-18 carbon atoms, or a combination thereof.

[0100] According to one embodiment of the present invention, wherein, the ring A, ring B, ring C and ring D are selected from benzene ring, naphthalene ring, fluorene ring, spirofluorene ring, silylfluorene ring, dibenzofuran ring, dibenzothiophene ring, dibenzoselenophene ring, phenanthrene ring, triphenylene ring, carbazole ring, anthracene ring, pyrene ring, or a combination thereof, the same or different each time they appear.

[0101] According to one embodiment of the present invention, wherein the ring A, ring B, ring C and ring D are selected from benzene ring, naphthalene ring, fluorene ring, dibenzofuran ring, dibenzothiophene ring, or a combination thereof, the same or different each time they appear.

[0102] According to one embodiment of the present invention, the compound has a structure represented by Formula 1-2:

[0103]

[0104] Among them, X1-X 15 Each occurrence is the same or different selection from CR x or N;

[0105] Each occurrence of Y1-Y8 is the same or different selection from CR y or N;

[0106] Each time Z1-Z8 appears, they are selected from CR z or N;

[0107] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0108] T is selected from a single bond, -O-, -S-, -CR'R"-, -NR'-, -SiR'R"-, -GeR'R"- or -CR'=CR"-;

[0109] R x , R y , R zR', R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0110] Adjacent substituent R x , R y , R z , R', and R" can be optionally linked to form a ring.

[0111] In this embodiment, “the adjacent substituent R x , R y , R z , R', R" can optionally be linked to form a ring", which is intended to indicate adjacent substituent groups, for example, two substituents R x Between the two substituents R y Between the two substituents R z Between the substituents R' and R", any one or more of these substituent groups can be connected to form a ring. Obviously, these substituents can also not be connected to form a ring.

[0112] According to one embodiment of the present invention, at least two adjacent substituents R y Connect to form a ring.

[0113] According to one embodiment of the present invention, at least two adjacent substituents R y They are linked to form a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic ring having 3 to 30 carbon atoms.

[0114] According to one embodiment of the present invention, at least two adjacent substituents Ry They are linked to form a substituted or unsubstituted aromatic ring having 6 to 12 carbon atoms.

[0115] According to one embodiment of the present invention, wherein said X1-X 15 Each occurrence is the same or different selection from CR x ; Each occurrence of Y1-Y8 is identical or different and is selected from CR y ; Z1-Z8 are selected from CR z .

[0116] According to one embodiment of the present invention, wherein the T is selected from a single bond, -O-, -S-, -CR'R"- or -NR'-.

[0117] According to one embodiment of the present invention, wherein the T is selected from a single bond or -CR'R"-, and the R', R" are the same or different each time they appear and are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, and combinations thereof.

[0118] According to one embodiment of the present invention, wherein said T is selected from a single bond.

[0119] According to one embodiment of the present invention, the compound has a structure represented by Formula 1-3:

[0120]

[0121] Among them, X1-X 15 Each occurrence is the same or different selection from CR x or N;

[0122] Each occurrence of Y1-Y8 is the same or different selection from CR y or N;

[0123] Each time Z1-Z8 appears, they are selected from CR z or N;

[0124] L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0125] R x , R y , R zEach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0126] Adjacent substituent R x , R y , R z Can optionally be linked to form a ring.

[0127] In this embodiment, “the adjacent substituent R x , R y , R z "can optionally be linked to form a ring" is intended to mean that adjacent substituent groups, for example, two substituents R x Between the two substituents R y Between the two substituents R z Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0128] According to one embodiment of the present invention, wherein the L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms, or a combination thereof.

[0129] According to one embodiment of the present invention, wherein the L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms, or a combination thereof.

[0130] According to one embodiment of the present invention, wherein, L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted silylfluorenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzoselenopheneylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted spirobifluorenylene, a substituted or unsubstituted anthrylenylene, a substituted or unsubstituted pyrenylene, or a combination thereof.

[0131] According to one embodiment of the present invention, wherein the L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

[0132] According to one embodiment of the present invention, wherein said L is selected from a single bond.

[0133] According to one embodiment of the present invention, wherein the R x , R y , R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0134] According to one embodiment of the present invention, wherein the R x , R y , R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

[0135] According to one embodiment of the present invention, wherein the R x , R y , R z Each occurrence is identically or differently selected from hydrogen or deuterium.

[0136] According to one embodiment of the present invention, X6, X7, X 10 and X 11 At least one of each occurrence is selected from CR x , and the R xEach occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0137] According to one embodiment of the present invention, X6, X7, X 10 and X 11 At least one of each occurrence is selected from CR x , and the R x Each occurrence is identically or differently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0138] According to one embodiment of the present invention, at least one of Z2, Z3, Z6 and Z7 is selected from CR z , and the R z Each occurrence is identically or differently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

[0139] According to one embodiment of the present invention, at least one of Z2, Z3, Z6 and Z7 is selected from CR z , and the R zEach occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0140] According to one embodiment of the present invention, at least one of Y2 and Y7 is selected from CR y , and the R y Each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0141] Adjacent substituent R y Can optionally be linked to form a ring.

[0142] According to one embodiment of the present invention, each occurrence of Y3 or Y6 is selected from CR z , and the R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbons having 6 to 30 carbon atoms, oxy group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0143] According to one embodiment of the present invention, the compound is selected from the group consisting of compound 1-1-1 to compound 1-1-178, compound 1-2-1 to compound 1-2-370, compound 1-3-1 to compound 1-3-22, and compound 1-4-1 to compound 1-4-22. For the specific structures of compound 1-1-1 to compound 1-1-178, compound 1-2-1 to compound 1-2-370, compound 1-3-1 to compound 1-3-22, and compound 1-4-1 to compound 1-4-22, please refer to claim 10.

[0144] According to one embodiment of the present invention, the hydrogen in the structures of Compounds 1-1-1 to 1-1-178, Compounds 1-2-1 to 1-2-370, Compounds 1-3-1 to 1-3-22, and Compounds 1-4-1 to 1-4-22 can be partially or completely replaced by deuterium.

[0145] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound described in any one of the aforementioned embodiments.

[0146] According to one embodiment of the present invention, the organic layer is an electron blocking layer or a hole transport layer.

[0147] According to one embodiment of the present invention, the organic layer is an electron blocking layer, and the compound is an electron blocking material.

[0148] According to one embodiment of the present invention, the thickness of the electron blocking layer is between 1 nm and 500 nm.

[0149] According to one embodiment of the present invention, an organic electroluminescent device is disclosed, comprising: an anode, a cathode, a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting layer, wherein the electron blocking layer comprises the compound described in any of the aforementioned embodiments.

[0150] According to one embodiment of the present invention, the electron blocking layer is in direct contact with the hole transport layer; the electron blocking layer is in direct contact with the light emitting layer.

[0151] According to one embodiment of the present invention, the hole transport layer comprises a hole transport material, and the hole transport material comprises a monotriarylamine compound or a bistriarylamine compound.

[0152] According to one embodiment of the present invention, a compound composition is disclosed, comprising the compound described in any one of the aforementioned embodiments.

[0153] Combination with other materials

[0154] The materials described herein for use in specific layers of organic light-emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. Patent Application No. US2016 / 0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0155] The materials described herein as being useful in specific layers of an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. patent application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0156] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more equipment conventional in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kosite's electrochemical workstation, Anhui Beiyi Ke's sublimator, etc.), and is tested for structure confirmation and characteristics using methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested using equipment conventional in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical testing system, life test system, Beijing Liangtuo's ellipsometer, etc.), and are tested using methods well known to those skilled in the art. Since those skilled in the art are aware of the use of the above-mentioned equipment, testing methods and other related content, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related content is no longer expanded in this patent.

[0157] Material synthesis example:

[0158] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0159] Synthesis Example 1: Synthesis of Compound 1-1-1

[0160] Step 1: Synthesis of Intermediate A

[0161]

[0162] Under N2 atmosphere, intermediate S1 (9 g, 36.3 mmol) and THF (72 mL) were added to a 500 mL two-necked flask, cooled to -75°C, n-BuLi (31 mL, 77.5 mmol) was added dropwise, and stirred for 1 h. A solution of intermediate S2 (6.5 g, 36.3 mmol) in THF (10 mL) was added dropwise, the reaction temperature was returned to room temperature and stirred for 3 h. The completion of the reaction was monitored by TLC, and the reaction was quenched with an appropriate amount of dilute hydrochloric acid. The liquids were separated, extracted with DCM, concentrated under reduced pressure, and purified by column chromatography to obtain solid intermediate A (6 g, yield 47.2%).

[0163] Step 2: Synthesis of Intermediate B

[0164]

[0165] Under N2 atmosphere, intermediate A (6 g, 17.2 mmol) and DCM (100 mL) were added to a 500 mL two-necked flask, and a solution of TFA (trifluoroacetic acid, 19.6 g, 172.0 mmol) in THF (10 mL) was added dropwise at room temperature. The mixture was stirred overnight at room temperature. The completion of the reaction was monitored by TLC, and the mixture was concentrated under reduced pressure and purified by column chromatography to obtain solid intermediate B (5 g, yield 87.7%).

[0166] Step 3: Synthesis of compound 1-1-1

[0167]

[0168] Under a nitrogen atmosphere, a 500 mL reaction flask was charged with intermediate S3 (3.66 g, 10 mmol), intermediate B (3.31 g, 10 mmol), lithium tert-butoxide (1.6 g, 20 mmol), Pd2(dba)3 (460 mg, 0.5 mmol), tBu3PHBF4 (0.3 g, 1.03 mmol), and xylene (80 mL). The temperature was raised to 150°C and the reaction was allowed to proceed for 15 h. The reaction was monitored for completion by TLC. The mixture was cooled to room temperature, filtered through celite, concentrated under reduced pressure, and purified by column chromatography to afford compound 1-1-1 (2.7 g, 40.8% yield) as a white solid. The product was confirmed to be the target product with a molecular weight of 661.22.

[0169] Synthesis Example 2: Synthesis of Compound 1-1-20

[0170] Step 1: Synthesis of Intermediate C

[0171]

[0172] Under N2 atmosphere, intermediate S4 (6 g, 16.5 mmol) and THF (48 mL) were added to a 500 mL two-necked flask, cooled to -75°C, n-BuLi (15 mL, 37.5 mmol) was added dropwise, and stirred for 1 h. A solution of intermediate S2 (3 g, 16.5 mmol) in THF (10 mL) was added dropwise, the reaction temperature was returned to room temperature and stirred for 3 h. The completion of the reaction was monitored by TLC, and the reaction was quenched with an appropriate amount of dilute hydrochloric acid. The layers were separated, extracted with DCM, concentrated under reduced pressure, and purified by column chromatography to give solid intermediate C (7.7 g, yield 100%).

[0173] Step 2: Synthesis of Intermediate D

[0174]

[0175] Under N2 atmosphere, intermediate C (7.7 g, 16.5 mmol) and DCM (120 mL) were added to a 500 mL two-necked flask, and a solution of TFA (18.8 g, 165 mmol) in THF (10 mL) was added dropwise at room temperature. The mixture was stirred at room temperature overnight. The completion of the reaction was monitored by TLC, and the mixture was concentrated under reduced pressure and purified by column chromatography to obtain solid intermediate D (4.3 g, yield 58.2%).

[0176] Step 3: Synthesis of compound 1-1-20

[0177]

[0178] Under a nitrogen atmosphere, a 500 mL reaction flask was charged with intermediate S3 (2.7 g, 7.36 mmol), intermediate D (3.29 g, 7.36 mmol), lithium tert-butoxide (1.6 g, 20 mmol), Pd2(dba)3 (460 mg, 0.5 mmol), tBu3PHBF4 (0.3 g, 1.03 mmol), and xylene (80 mL). The temperature was raised to 150°C and the reaction was allowed to proceed for 15 h. The reaction was monitored for completion by TLC. The mixture was cooled to room temperature, filtered through celite, concentrated under reduced pressure, and purified by column chromatography to afford compound 1-1-20 (1.1 g, 19.2% yield) as a white solid. The product was confirmed to be the desired product with a molecular weight of 777.29.

[0179] Those skilled in the art should be aware that the above preparation methods are only two illustrative examples, and those skilled in the art can obtain other compound structures of the present invention by improving them.

[0180] The preparation method of the organic electroluminescent device is not limited. The preparation method of the following device embodiment is only an example and should not be understood as limiting. Those skilled in the art can reasonably improve the preparation method of the following device embodiment based on existing technology.

[0181] Device Examples

[0182] Device Example 1: Preparation of an organic electroluminescent device.

[0183] First, a 0.7 mm thick glass substrate with a pre-patterned The thick indium tin oxide (ITO) is used as the anode. After washing the substrate with deionized water and detergent, the ITO surface is treated with oxygen plasma and UV ozone. Subsequently, the substrate is dried in a glove box to remove moisture and placed on a holder and transferred to the vacuum chamber. The organic layer specified below is placed in a vacuum of about 10 -6 Torr's case The anode layer was deposited sequentially by vacuum thermal evaporation at a rate of: first, compound HT-1 and compound HT-2 were simultaneously deposited as a hole injection layer (HIL, weight ratio 97:3, ), the evaporated compound HT-1 was used as a hole transport layer (HTL, ), evaporate the compound 1-1-1 of the present invention as an electron blocking layer (EBL, ), then simultaneously evaporate compound H-1, compound H-2 and compound GD as the light-emitting layer (EML, weight ratio 48:48:4, ). Evaporation compound HB as hole blocking layer (HBL, ), compound ET and Liq were co-deposited as electron transport layer (ETL, weight ratio 40:60, ), evaporation The thickness of Liq is used as the electron injection layer (EIL, Finally, aluminum is evaporated as the cathode. ). The device was then transferred back to the glove box and encapsulated with a glass cover slip to complete the device.

[0184] Device Example 2

[0185] Device Example 2 was prepared in the same manner as Device Example 1, except that the present compound 1-1-20 was used instead of the present compound 1-1-1 in the electron blocking layer (EBL).

[0186] Device Comparative Example 1

[0187] Device Comparative Example 1 was prepared in the same manner as Device Example 1, except that Compound EB1 was used in place of the present compound 1-1-1 in the electron blocking layer (EBL).

[0188] Device Comparative Example 2

[0189] Device Comparative Example 2 was prepared in the same manner as Device Example 1, except that Compound EB2 was used in place of the present compound 1-1-1 in the electron blocking layer (EBL).

[0190] The detailed device layer structures and thicknesses are shown in Table 1. For layers using more than one material, the different compounds are doped in the weight ratios listed.

[0191] Table 1 Partial device structures of Examples 1-2 and Comparative Examples 1-2

[0192]

[0193]

[0194] The material structure used in the device is as follows:

[0195]

[0196]

[0197] At 10 mA / cm 2 The current efficiency (CE), power efficiency (PE), external quantum efficiency (EQE) and voltage (V) of Examples 1-2 and Comparative Examples 1-2 were measured at a current density of 80 mA / cm 2 The LT97 lifetimes of Examples 1-2 and Comparative Examples 1-2 were measured at different current densities. For a more intuitive comparison, the LT97 lifetime of Comparative Example 1 was set to 100%. The LT97 lifetimes of Examples 1, 2, and Comparative Example 2 were calculated relative to Comparative Example 1. These data are recorded and presented in Table 2.

[0198] Table 2 Device data of Examples 1-2 and Comparative Examples 1-2

[0199]

[0200] discuss:

[0201] The present invention compound 1-1-1 and comparative example compound EB1 both have spiro silicon fluorene and nitrogen-containing spiro ring structure simultaneously, and the difference is only that the connection position of spiro silicon fluorene is different from that of nitrogen-containing spiro ring, but the device performance difference is very obvious, as shown in Table 2 data, compared with Comparative Example 1, the voltage of Example 1 is significantly reduced by 0.75V, and at the same time, the current efficiency is greatly improved by 1.8 times, the power efficiency is greatly improved by 2.4 times, the external quantum efficiency is greatly improved by 1.8 times, and the life span is greatly improved by 5.7 times. The difference between the present invention compound 1-1-1 and comparative example compound EB2 is only that the nitrogen-containing spiro ring is connected to spiro silicon fluorene in the present invention compound, and the nitrogen-containing spiro ring is connected to silicon fluorene in comparative example compound EB2, but the device performance difference is obvious, as shown in Table 2 data, the voltage and efficiency (CE, PE, EQE) of Comparative Example 2 are already at a higher level, compared with Comparative Example 2, the voltage of Example 1 is further reduced by 0.13V, and efficiency (CE, PE, EQE) is substantially equivalent to it, and more importantly, the life span is greatly improved by 3.6 times.

[0202] The above data show that the compound of the present invention, because it has both a spirosilane structure and a nitrogen-containing spirocyclic structure and the two have specific connection positions, can significantly reduce the device voltage, greatly improve the device efficiency or maintain high device efficiency, and especially can greatly improve the device life, and can provide better overall performance in the device.

[0203] The compound 1-1-20 having an additional fused structure on the nitrogen-containing spiro structure of the present invention also has very excellent performance when applied to the device. It can be seen from the data in Table 2 that compared with Comparative Example 1, the voltage of Example 2 is significantly reduced by 0.92 V, the current efficiency is greatly improved by 1.63 times, the power efficiency is greatly improved by 2.33 times, the external quantum efficiency is greatly improved by 1.6 times, and the lifespan is greatly improved by 4.78 times; compared with Comparative Example 2, the voltage of Example 2 is further reduced by 0.3 V, and the efficiency (CE, PE, EQE) remains at a high level substantially equivalent to that thereof. More importantly, the lifespan is greatly improved by 2.96 times, which once again proves the unique advantages of the compound having the structure of Formula 1 of the present invention.

[0204] In summary, the compound having a specific structure represented by Formula 1 of the present invention can be used in organic electroluminescent devices to reduce device voltage, improve device efficiency or maintain high device efficiency, and in particular can significantly increase device life, provide better overall device performance, and has very broad application prospects.

[0205] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. A compound having a structure represented by Formula 1: in, X1-X 15 Each occurrence is the same or different selection from CR x or N; Ring A and Ring B are identical or different at each occurrence and are selected from an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof; R y Each occurrence of the same or different means mono-, poly- or no-substitution; R1, R2 are the same or different at each occurrence and are selected from substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 ring carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or a combination thereof; R1 and R2 can optionally be linked to form a ring; L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; T is selected from a single bond, -O-, -S-, -CR'R"-, -NR'-, -SiR'R"-, -GeR'R"- or -CR'=CR"-; R x , R y R', R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R x , R y , R', and R" can be optionally linked to form a ring.

2. The compound according to claim 1, wherein The compound has a structure represented by Formula 1-1: Among them, X1-X 15 Each occurrence is the same or different selection from CR x or N; Ring A and Ring B are identical or different at each occurrence and are selected from an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof; Ring C and Ring D are identical or different at each occurrence and are selected from a saturated carbocyclic ring having 3 to 20 carbon atoms, an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof; R y , R z Each occurrence of the same or different means mono-, poly- or no-substitution; L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; T is selected from a single bond, -O-, -S-, -CR'R"-, -NR'-, -SiR'R"-, -GeR'R"- or -CR'=CR"-; R x , R y , R z R', R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R x , R y , R z , R', and R" can be optionally linked to form a ring.

3. The compound according to claim 2, wherein Ring A, Ring B, Ring C and Ring D are identically or differently selected at each occurrence from an aromatic ring having 6 to 18 carbon atoms, a heteroaromatic ring having 3 to 18 carbon atoms, or a combination thereof; Preferably, ring A, ring B, ring C and ring D are identically or differently selected from a benzene ring, a naphthalene ring, a fluorene ring, a dibenzofuran ring, a dibenzothiophene ring, or a combination thereof at each occurrence.

4. The compound according to claim 3, wherein The compound has a structure represented by Formula 1-2: Among them, X1-X 15 Each occurrence is the same or different selection from CR x or N; Each occurrence of Y1-Y8 is the same or different selection from CR y or N; Each time Z1-Z8 appears, they are selected from CR z or N; L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; T is selected from a single bond, -O-, -S-, -CR'R"-, -NR'-, -SiR'R"-, -GeR'R"- or -CR'=CR"-; R x , R y , R z R', R" are each identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituent R x , R y , R z , R', and R" can be optionally linked to form a ring.

5. The compound according to claim 4, wherein The X1-X 15 Each occurrence is the same or different selection from CR x ; Each occurrence of Y1-Y8 is identical or different and is selected from CR y ; Z1-Z8 are selected from CR z .

6. The compound according to claim 1, 2 or 4, wherein Said T is selected from a single bond, -O-, -S-, -CR'R"- or -NR'-; Preferably, T is selected from a single bond or -CR'R"-, and R', R" are identical or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; More preferably, said T is selected from a single bond.

7. The compound according to claim 1, 2 or 4, wherein The L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms, or a combination thereof; Preferably, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted silylfluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzoselenopheneylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyrenylene group, or a combination thereof; More preferably, said L is selected from a single bond.

8. The compound according to claim 4, wherein The R x , R y , R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; Preferably, the R x , R y , R z Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, and combinations thereof.

9. The compound according to claim 4, wherein X6, X7, X 10 and X 11 At least one of each occurrence is selected from CR x , and / or at least one of Z2, Z3, Z6 and Z7 is selected from CR z , and the R x , R z Each occurrence is identically or differently selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

10. The compound according to claim 1, wherein The compound is selected from the group consisting of compound 1-1-1 to compound 1-1-178, compound 1-2-1 to compound 1-2-370, compound 1-3-1 to compound 1-3-22, and compound 1-4-1 to compound 1-4-22: Optionally, hydrogen in the structures of Compound 1-1-1 to Compound 1-1-178, Compound 1-2-1 to Compound 1-2-370, Compound 1-3-1 to Compound 1-3-22, and Compound 1-4-1 to Compound 1-4-22 can be partially or completely replaced by deuterium.

11. An organic electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 to 10.

12. The organic electroluminescent device according to claim 11, wherein The organic layer is an electron blocking layer or a hole transport layer; Preferably, the organic layer is an electron blocking layer, and the compound is an electron blocking material.

13. A compound composition comprising the compound according to any one of claims 1 to 10.

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